Chianti, Florence & Seaside Villages

Tuscany & the Cinque Terre Cultural Walking Tour

7 DaysStarting at $6,195


Drinking in the sunset and the Chianti at our friend Marco's farmhouse, we decided that a Tuscany walking tour couldn't be improved upon. Since he's a staunch Tuscan, he surprised us by saying, "Then you've never been to the Cinque Terre." So we went. They're not far, these five once almost unreachable villages that grow out of rock along the Ligurian Sea. For centuries, a connecting footpath was their lifeline, but for us it's the scenic route into a remote and vibrant coastal culture. Beforehand, we spend three nights in the parts of Tuscany we love best…complete with hilltowns that rise out of silver-green olive groves, homemade prosciutto and potato ravioli and the sunny vineyards of Chianti. Throughout, we'll explore the art history, and savor the food and wine. But in the end, will you prefer walking tours in Tuscany or the Cinque Terre? The good news is that because this trip gives you both, you don't have to decide.

Classic Journeys’ tour to Tuscany and the Cinque Terre is our favorite luxury walking experience.”
Forbes Magazine


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Gather in Florence, where a short journey into Chianti leads to a private visit and tasting at one of the famed wineries, followed by a scenic walk to our hotel, a historic villa that dates to the 16th century and is owned by a count and countess.

Walk past silvery olive groves to visit a shepherd who shows how he makes sheep's-milk cheeses…and a chance to sample some of the traditional specialties.

Follow a footpath in the lovely Chianti hills, to a vineyard walk that ends with a home-cooked lunch and wine-tasting in the private cellars of Castello della Paneretta.

Spot San Gimignano, fortified with more than a dozen medieval towers, shimmering in the near distance as we approach along a rural footpath.

Journey along the Apuane mountains to Santa Margherita, where our hotel overlooks the Ligurian Sea.

Walk to the colorful, isolated villages of the Cinque Terre — Monterosso, Vernazza, Corniglia, Manarola and Rio Maggiore — with time out for shopping or a picnic. (Or skip the walking, and take a little coastal train that runs between the villages.)

Explore the tiny monastery of San Fruttuoso reachable only by foot or boat after visiting iconic Portofino.

Cap off an evening in Florence with a memorable dinner at our favorite trattoria, where in one meal we enjoy the whole tapestry of Tuscan cuisine.

Skip the lines to see Michelangelo's David as part of a guided walk in Florence that provides an insider's view of the famed Renaissance city.

Wandering the ancient streets to see and learn about Brunelleschi's incredible dome, the Ponte Vecchio, and Piazza della Signoria.

Graze through San Lorenzo, the Florentine's main market, with its pyramids of produce, olives, breads, meats and more.

Download Full Daily Itinerary


  • Starting Point:

    Florence – 1:00 pm – Lobby of Antica Torre Di Via Tornabuoni Hotel
  • Ending Point:

    Florence – 1:00 pm – Lobby of Antica Torre Di Via Tornabuoni Hotel
Itinerary Map

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Dates & Prices

The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, “Classic Journeys provides unbeatable access to experiences around the globe.” Here’s what that access means for you.
  • Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in Tuscany and along the coastal towns of Cinque Terre.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, sharing their lifelong connections as well as engaging anecdotes about Italian history and culture.
  • Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like skipping the lines to see Michelangelo’s David in Florence, visiting with a shepherd and tasting his sheep’s-milk cheeses and strolling through a vineyard with the owners in Tuscany.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including a historic villa that dates to the 16th century and is owned by a count and countess.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.


We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

Villa Le Barone

This historic home dates to the 16th century, and your hosts are a count and countess. Its rooms have wood-beamed ceilings and antiques. The property boasts lovely gardens, a new saltwater infinity pool, and a terrace for sunning and Chianti sipping.

Grand Hotel Miramare pool

Grand Hotel Miramare

One of the first grand hotels in the region, this property is a Leading Hotel of the World. It offers all of the luxurious comfort you expect…plus a pool that overlooks the scenic promenade to Portofino.

Antica Torre Di Via Tornabuoni

Originally a palace of the Guelf family, this historic hotel in the heart of Florence is known for its attentive service. The rooftop terraces offer remarkable views of the entire city. Rooms are decorated in elegantly understated Florentine style.

What’s Included

  • Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
  • All breakfasts, 1 lunch and 5 dinners
  • Full-time experienced guide(s) who are with you throughout the trip, handle behind-the-scenes logistics 
  • Admissions to sites and other scheduled events as noted in the detailed daily itinerary
  • Gratuities for hotels, meals and baggage
  • All land transportation during the trip

Above & Beyond Benefits

Perfect Pairings Dinners

  • A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.

Invisible Check-In

  • When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.

Privileged Access Events

  • One-of-a-kind access to remarkable people, places and activities arranged just for you.

Wine on Us

  • In many regions, we uncork wonderful local wines at every dinner, compliments of Classic Journeys.

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